Triethylamine → HCID 9828632, compound

HRID 1608497Notes

Reaction equation

HRID 1608497 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:16][O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([Br:28])=[CH:20][C:19]=1[C:29]([OH:31])=O.[Cl:32][C:33]1[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=1[N:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][NH2:48])[CH2:42][CH2:41]1>O1CCCC1>[Br:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([O:17][CH3:16])=[C:19]([C:29]([NH:48][CH2:47][CH2:46][N:43]2[CH2:42][CH2:41][N:40]([C:34]3[CH:35]=[CH:36][CH:37]=[C:38]([Cl:39])[C:33]=3[Cl:32])[CH2:45][CH2:44]2)=[O:31])[CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 12084040HCID 12084040, compoundHCID 20086618HCID 20086618, compound

Product 1

HCID 9828632HCID 9828632, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (1.24 mL, 8.87 mmol) and isobutyl chloroformate (0.50 mL, 3.9 mmol) are added to 1-methoxy-4-bromo-2-naphthoic acid (European Published Patent Application EP 0 539 281A1) (1.0 g, 3.55 mmol) in dry tetrahydrofuran (20 mL) at 0° C. and allowed to stir for 1 hour. To this mixed anhydride is added 4-(2,3-dichlorophenyl)-l-piperazineethanamine (0.97 g, 3.55 mmol) in dry tetrahydrofuran (5 mL) and stirring continued for 18 hours, gradually allowing the mixture to warm to room temperature. The reaction mixture is washed with saturated sodium chloride (NaCl), dried (sodium sulfate), and concentrated to give 0.27 g of the title compound as a white solid; mp 137° C.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. washThe reaction mixture is washed with saturated sodium chloride (NaCl)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0cc5e3853b40480b8b2fc5f462892963
Source dataset
uspto-grants-1995_03
Patent number
US05395835

Reaction notes

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